Pyridine-derivatives

Application of 153034-88-9 ,Some common heterocyclic compound, 153034-88-9, molecular formula is C6H5ClIN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 2-chloro-4-iodo-3-methylpyridine (303 mg, 1.20 mmol) (Aldrich, catNo.724092), phenylboronic acid (160 mg, 1.32 mmol) (Aldrich, catNo.78181) and sodium carbonate (317 mg, 2.99 mmol) in tert-butyl alcohol (10 mL) and water (6 mL) was added Pd-127 (181 mg, 0.239 mmol). The resulting mixture was purged with N2, and then heated at 80 C. for 2 h. The reaction mixture was diluted with methylene chloride, washed with saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 10 to 20% ethyl acetate in hexanes to give the desired product (225 mg, 92%). LCMS calculated for C12H11ClN (M+H)+: m/z=204.2; found 204.2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Li, Zhenwu; Wu, Liangxing; Yao, Wenqing; (48 pag.)US2017/320875; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Methoxy-4,6-dimethylnicotinonitrile

To a cooled (ice water bath) solution of 2-methoxy-4,6-dimethylnicotinonitrile (10 g, 61.7 mmol) in Et2O (200 mL) was added dropwise 1 M LiAIH4 in Et2O (123 mL, 123 mmol). The ice bath was removed and the reaction mixture was stirred at r.t. for 16 h. The reaction mixture was cooled in an ice water bath and quenched with a mininum amount of water (until no more hydrogen was generated). The reaction was filtered and the insoluble material was washed with 10: 1 DCM/MeOH. The combined organic filtrates were concentrated. The residue was purified via column chromatography (0 – 30% MeOH/DCM; 100 g-HP- silica gel column) to give (2-methoxy-4,6-dimethylpyridin-3- yl)methanamine (8.9 g) as a yellowish semi-solid.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BRACKLEY, III, James A.; GRAVES, III, Alan Peterson; KNIGHT, Steven David; MCNULTY, Kenneth C.; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (114 pag.)WO2017/2064; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H7BrN2O

[00210] To a stirred solution of triphosgene (1 eq, 0.83 mmol) in DCM (16 ml_) at -20 C and under an atmosphere of N2 was added a solution of 2-bromo-6-methoxy-pyridin-4- ylamine (1 eq, 0.83 mmol) in DCM (6 ml_) followed by triethylamine (2.5 eq, 2.08 mmol). The reaction was stirred at -20 C for 15 mins then allowed to warm to RT and stirred at RT for 30 mins. The reaction was cooled to -20 C and a solution of ((1S,3R)-(3-amino-cyclopentyl)- carbamic acid benzyl ester in dry DCM (3 ml_) was added and the reaction stirred at -20 C for 15 mins then at RT for 90mins. More triethylamine (2 eq, 1.66 mmol) was added and the reaction was at RT for 1 h. The reaction was quenched with methanol and concentrated in vacuo. The crude was purified by column chromatography to benzyl N-[(1S,3R)-3-[(2-bromo- 6-methoxy-4-pyridyl)carbamoylamino]cyclopentyl]carbamate (311 mg, 81 %) as a light yellow gum. AnalpH2_MeOH_4min, Rt: 3.21 min; m/z 463/465[M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 1196152-34-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 912369-42-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 912369-42-7, name is Methyl 3-((tert-butoxycarbonyl)amino)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 3-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate (1.53 g, 6.06 mmol) was dissolved in AcOH (30 mL). PtO2 (770 mg) was added and the mixture was stirred under H2 atmosphere (5 bar) for 12 hours. The catalyst was filtered off, the solvent was evaporated and the residue taken up with DCM (50mL) and washed with NaHCO3 aqueous saturated solution. The organic phase was concentrated to give methyl 3-{[(tert-butoxy)carbonyl]amino}piperidine-2- carboxylate (1.42 g, 91 % yield) as diastereoisomeric mixture.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 912369-42-7, Methyl 3-((tert-butoxycarbonyl)amino)picolinate.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Product Details of 1111637-94-5

Example B-6: Preparation of (2S)-1-(4-(3-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-isopropyl- 1 H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-6)B-6-1 B-6-2 B-6-3Preparation of 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2)B-6-1 B-6-2 To a solution of 5-bromo-3-methyl-1 H-pyrrolo[2,3-b]pyridine (B-6-1 ) (1.2 g, 5.68 mmol) in THF (30 mL) was added NaH (0.34 g, 8.5 mmol) under N2 at O0C, 4-bromophenylsulfonyl chloride (1.2 g, 6.8 mmol) was added 30 minutes later. The mixture was stirred at room temperature for 1.5 h. TLC (Petroleum ether: EtOAc = 5:1 ) showed that the reaction was complete. Saturated aqueous NaCI (10 mL) was added, and the mixture was filtered to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (B-6-2) (0.8 g) as a white solid. The organic layer was separated from the filtrate, concentrated to 8 mL, then filtered to give 5-bromo-1-(4-bromophenylsulfonyl)-3-methyl-1 H-pyrrolo[2,3-b]pyridine (0.5 g). Two batches were combined to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2) (1.3 g, 65.2%) as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 1111637-94-5.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885326-88-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 885326-88-5, name is Methyl 6-amino-4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a microwave tube was added methyl 6-amino-4-bromopicolinate (CAS: 885326-88-5, Vendor: PharmBlock, 231 mg, 1.00 mmol), THF (3 mL) and LiBH4 (2 M in THF, 1 mL, 2.00 mmol). After being stirred at 65 C for 2 hrs under microwave, the reaction was quenched by adding Na2S04 * 10H2O and the mixture was stirred at rt for another hour. Then it was filtered through celite and the filtrate was concentrated to give compound 45a (230 mg) as a crude oil. MS: calc’d 203 (MFP), measured 203 (MH+).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 885326-88-5, Methyl 6-amino-4-bromopicolinate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LIU, Haixia; SHEN, Hong; ZHU, Wei; HU, Taishan; ZHANG, Zhisen; ZHANG, Zhiwei; DEY, Fabian; WANG, Xiaoqing; (89 pag.)WO2019/238629; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23628-31-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 6. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(2- (trifluoromethyl)phenyl)benzo[d]oxazole-7-carboxamide (Compound 125) : Step 1) Preparation of ethyl 6-aminopicolinate (20): 19 20To a solution of 2-amino-6-pyridinecarboxyric acid (19; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 20 (5.5 g, 76%).

According to the analysis of related databases, 23628-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; WO2010/19606; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 910656-00-7, 4-Amino-N-methylnicotinamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C7H9N3O, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9N3O

4-Amino-Lambda/-methyl-3-pyridinecarboxamide (200 mg; may be prepared as described in intermediate 121 ) was dissolved in DMF (20.00 ml_). DMAP (8.08 mg), N,N- diisopropylethylamine (0.462 ml.) and chloroacetyl chloride (0.212 ml.) were added at room temperature under stirring. The mixture was heated in the microwave for 10 min at100 0C. The mixture was diluted with EtOAc (10 ml) and washed with water and brine ( x3). Organics were dried over sodium sulphate, filtered and the solvent was evaporated to afford the crude product that was purified by silica chromatography to afford the title compound (100 mg, 0.395 mmol). m/z [M+H]+: 228.1 / 230.1. Retention time 0.44 min (LC/MS method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,910656-00-7, 4-Amino-N-methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem